Patent GB-729424-A (GB)
Title: Improvements in or relating to oil-soluble polymeric compounds
Inventor: ARVIN JAMES AUGUSTUS
IPC: C08G63/48
Filed: 1951-01-18
Abstract: Alkyd resins are prepared by heating together at least one polycarboxylic acid, at least one polyhydric alcohol, and at least one unsaturated monocarboxylic acid, at least part of the polyhydric alcohol being an aryl polyoxyalkoxy ether alkanol. Suitable polycarboxylic acids or their corresponding anhydrides are saturated aliphatic dicarboxylic acids with 4-36 carbon atoms, e.g. succinic, methyl-succinic, mono-mercaptosuccinic, glutaric, adipic, methyl-adipic, pimelic, mercaptopimelic, suberic, azelaic, sebacic, mercapto-sebacic acid, and dichloro-succinic; unsaturated aliphatic acids, e.g. maleic, fumaric, citraconic, mesaconic, itaconic, aconitic, glutaconic and acetylene dicarboxylic acid; hydroxy acids, e.g. citric, tartaric and malic; cyclic acids, e.g. phthalic, isophthalic, terephthalic, naphthalic, camphoric, diphenic and diene adducts, e.g. from terpenes, styrene or rosin.  Suitable unsaturated monobasic acids are those derived from drying or semi-drying oils. These may be used as their partial or total esters with polyhydric alcohols. The monobasic acid may be wholly or partly replaced by rosin or rosin acids, modified rosin acids or tall oil.  The aryl polyoxyalkoxy ether alkanols are prepared by reacting an alkylene halohydrin or an alkylene oxide with a polyhydric phenol, e.g. resorcinol, hydroquinone, catechol, orcinol, phloroglucinol, pyrogallol, hydroxyquinol, polyhydric, multi-nuclear phenols, such as diphenylol propane, prepared by condensation of a phenol or a naphthol with an aldehyde or ketone.  Typical alkanols are bis - (b - hydroxyethoxyethoxyphenyl) methane; bis-(hydroxypropoxypropoxy-o-tolyl) methane; bis - (hydroxypropoxypropoxyphenyl) dimethyl methane; 4-hydroxypropoxypropoxyphenyl-41-hydroxypropoxyphenyl -dimethylmethane; tris-(hydroxyethoxyphenyl) methane; 4,41 - bis-hydroxyethoxy)-diphenyl.  The reaction mixture may also include polyhydric alcohols usually employed in making alkyd resins, e.g. ethylene glycol, glycerol, pentaerythritol.  The products may be mixed with drying oils, other resins natural or synthetic, cellulose derivatives, pigments, driers, and plasticizers.  The reaction may be performed with a solvent which aids removal of water.  In the examples resins were prepared from (1) glycerine heated with dehydrated castor oil in presence of lithage.  Phthalic anhydride, bis - (hydroxypropoxy - phenyl)-dimethyl methane and xylene were added and reaction continued under reflux.  The product was thinned with xylene; (2) bis-(hydroxypropoxyphenyl) - dimethyl methane, maleic anhydride and linseed oil fatty acids.  Dissolved in xylene with lead and cobalt naphthenates it gave a coating composition; (3), (4) and (5) bis-(hydroxypropoxyphenyl) dimethyl methane, fumaric acid, and dehydrated castor oil fatty acids or linseed oil fatty acids. Many other examples are given, some of them exemplifying the manufacture and use of 1,3-bis - (hydroxyethoxy) - benzene; tris - (hydroxyethoxy) benzene; 2,4,21,41-tetrakis-(b -hydroxyethoxy) - diphenyl methane; bis - (3,4,5 - tri - hydroxytriethoxyphenyl) methane; 2,4,21,41-tetrakis-(b -hydroxyethoxy) biphenyl; 4,41,411-tris-(hydroxyethoxyphenyl) methane; and the condensation product of ethylene chlorhydrin with bis-(hydroxynaphthyl) methane. Specification 696,585, [Group IV (b)], is referred to.